A thioether-directed palladium-cleavable linker for targeted bioorthogonal drug decaging

Chemical Science
Benjamin J StentonGonçalo J L Bernardes

Abstract

We describe the development of a bifunctional linker that simultaneously allows site-specific protein modification and palladium-mediated bioorthogonal decaging. This was enabled by a thioether binding motif in the propargyl carbamate linker and a readily available palladium complex. We demonstrate the efficiency of this reaction by controlled drug release from a PEGylated doxorubicin prodrug in cancer cells. The linker can be easily installed into cysteine bearing proteins which we demonstrated for the construction of an anti-HER2 nanobody-drug conjugate. Targeted delivery of the nanobody drug conjugate showed effective cell killing in HER2+ cells upon palladium-mediated decaging.

References

Sep 10, 2005·Nature Biotechnology·Philipp Holliger, Peter J Hudson
Jul 3, 2008·Journal of the American Chemical Society·Yuya A LinBenjamin G Davis
Jan 6, 2011·Chemical Communications : Chem Comm·Christopher D Spicer, Benjamin G Davis
Apr 12, 2011·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Ilse VaneyckenVicky Caveliers
Dec 17, 2011·Angewandte Chemie·Gonçalo J L BernardesDario Neri
Nov 28, 2013·Angewandte Chemie·Ron M VersteegenMarc S Robillard
Feb 1, 2014·Journal of the American Chemical Society·Duy P NguyenJason W Chin
May 29, 2014·Journal of Medicinal Chemistry·Jason T WeissAsier Unciti-Broceta
Jun 27, 2014·Journal of Medicinal Chemistry·John M Lambert, Ravi V J Chari
Aug 21, 2014·Angewandte Chemie·Timo VölkerEric Meggers
Nov 5, 2014·Nature Chemical Biology·Jie LiPeng R Chen
Oct 30, 2015·Nature·Ekaterina V VinogradovaStephen L Buchwald
Feb 18, 2016·Nature Chemical Biology·Jie Li, Peng R Chen
Oct 27, 2016·Nature Communications·Barbara BernardimGonçalo J L Bernardes
Nov 1, 2016·Journal of the American Chemical Society·Jie WangPeng R Chen
Jun 7, 2017·Chemical Communications : Chem Comm·Eugenio IndrigoMark Bradley
Jul 1, 2017·Chemical Society Reviews·B L OliveiraG J L Bernardes
Apr 16, 2015·Chemical Science·Anaëlle Dumas, Patrick Couvreur
Jul 13, 2017·Nature Communications·Miles A MillerRalph Weissleder

❮ Previous
Next ❯

Citations

Nov 25, 2018·Nature Protocols·Barbara BernardimGonçalo J L Bernardes
Jul 12, 2019·Chemical Society Reviews·Jonathan D BarghDavid R Spring
Mar 13, 2020·Angewandte Chemie·Soraya Learte-AymamíJosé L Mascareñas
Jul 17, 2020·Chemical Communications : Chem Comm·Tiantian WuYangzhong Liu
Oct 18, 2019·Nature Catalysis·María Sancho-AlberoAsier Unciti-Broceta
Jan 30, 2019·Chembiochem : a European Journal of Chemical Biology·Julian TuRaphael M Franzini
Aug 8, 2019·Angewandte Chemie·Tiantian WuBaoquan Ding
Aug 21, 2020·ChemistryOpen·Youshan Li, Hua Fu
Dec 14, 2018·Chemical Science·Thomas L BrayAsier Unciti-Broceta
Apr 1, 2020·Angewandte Chemie·Sebastian PomplunBradley L Pentelute
Jul 7, 2020·Angewandte Chemie·Joan Miguel-ÁvilaJosé L Mascareñas
Oct 8, 2020·Chemical Society Reviews·Eloah LatocheskiJosiel B Domingos
Sep 30, 2020·Chemistry : a European Journal·Paolo DestitoJosé L Mascareñas
Jan 21, 2021·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Manman LiuYangzhong Liu
Nov 5, 2020·Current Opinion in Chemical Biology·Melissa O N van de L'IsleAsier Unciti-Broceta
May 9, 2021·Journal of Controlled Release : Official Journal of the Controlled Release Society·Sandeep Surendra PanikarPedro Salas
Jun 2, 2021·Journal of the American Chemical Society·Mary A WaddingtonAlexander M Spokoyny
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Stephanie BaahKhondaker Miraz Rahman
Jul 9, 2021·ACS Central Science·Jie WangPeng R Chen
Aug 2, 2021·Advanced Drug Delivery Reviews·Wenjie WangVincent M Rotello
Aug 9, 2021·Bioorganic & Medicinal Chemistry·Boris Lozhkin, Thomas R Ward
Oct 4, 2019·Journal of the American Chemical Society·Xin WangPeng R Chen
May 28, 2020·Journal of the American Chemical Society·Bruno L OliveiraGonçalo J L Bernardes
Mar 21, 2019·Journal of the American Chemical Society·Cristian VidalJosé L Mascareñas
Feb 21, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Dongxiang XueHouchao Tao
Jul 31, 2019·Journal of the American Chemical Society·Alec H ChristianF Dean Toste
Aug 23, 2021·Bioorganic & Medicinal Chemistry·Tsung-Che Chang, Katsunori Tanaka
Nov 6, 2021·Angewandte Chemie·Juraj KončGonçalo J L Bernardes

❮ Previous
Next ❯

Methods Mentioned

BETA
pull-down
Fluorescence

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Annals of the New York Academy of Sciences
K HongD Papahadjopoulos
Annals of Oncology : Official Journal of the European Society for Medical Oncology
A FabiF Cognetti
Chemical Communications : Chem Comm
Yuanzeng MinYangzhong Liu
Nature Methods
Allison Doerr
© 2022 Meta ULC. All rights reserved